Pyridine → 5,6-Dichloro-2-[4-methoxy-3-(thiophene-2-sulfonylamino)-phenyl]-benzoimidazole-1-carboxylic acid benzyl ester

HRID 25500

Reaction equation

HRID 25500 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=[C:12]1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([NH2:30])[CH:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[S:42](Cl)(=[O:44])=[O:43]>O>[CH2:1]([O:8][C:9]([N:11]1[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=[C:12]1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([NH:30][S:42]([C:38]2[S:37][CH:41]=[CH:40][CH:39]=2)(=[O:44])=[O:43])[CH:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 855182-Thiophenesulfonyl chlorideHCID 102751152-(3-Amino-4-methoxy-phenyl)-5,6-dichloro-benzoimidazole-1-carboxylic acid benzyl ester

Product 1

HCID 207608855,6-Dichloro-2-[4-methoxy-3-(thiophene-2-sulfonylamino)-phenyl]-benzoimidazole-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Amino-4-methoxy-phenyl)-5,6-dichloro-benzoimidazole-1-carboxylic acid benzyl ester from Step C was mixed with pyridine (5 mL) and 2-thienylsulfonyl chloride (0.1283 g, 0.7 mmol) was added. The mixture was allowed to stand overnight. Water (100 mL) was added to the reaction mixture and the product crystallized within 5 hours. The solid was then collected by filtration and triturated with 1/1, hexanes/ethyl acetate (0.2 g), mp 195-198° C.

Workup

  1. additionwas added
  2. customthe product crystallized within 5 hours
  3. filtrationThe solid was then collected by filtration
  4. customtriturated with 1/1, hexanes/ethyl acetate (0.2 g), mp 195-198° C.

Sources & evidence

ORD record
ord-e88a56c1ea754f9188e31ee79851c503
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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